Ozzy begins suffering from insomnia. He eventually undergoes testing with a sleep disorder expert to determine the cause. Jack gets a tattoo of a cross on his chest, but Ozzy and Sharon do not like it.

The family tries to decide where to go on vacation. Sharon turns down Fiji because none of the hotels meet her standards, while Ozzy nixes a number of other locations for various reasons. Sharon ultimately decides on Hawaii, although Ozzy is still reluctant to go. Meanwhile, Kelly wins a major role in a television pilot. She must miss out on the family's vacation to go to Vancouver for filming.

Ozzy, Sharon and Jack head to Hawaii for their vacation. Ozzy continues to be miserable for a while, but cheers up following a private luau. Jack goes diving in a shark cage. His friends invite strippers to the luau, and behave in ways that embarrass him. The traveling party winds up leaving without Jack's friends when they fail to show up on time for their flight.

Kelly irritates her mother by getting a lip ring. Ozzy and Jack are convinced that Kelly's erratic behavior and chronic illness are the result of drug use, but Sharon refuses to hear of it. Kelly eventually admits the truth to Sharon and enters rehab. Ozzy and Sharon don't believe she will stay at the facility for long.

Kelly struggles to adjust to life in rehab, and frequently calls home requesting various personal belongings. She wants to leave, but Jack urges her to tough it out. Jack celebrates both his birthday and a year of sobriety. Kelly arrives home and becomes frustrated by the curfew and other rules she must follow. She clashes with her mother often, and accuses Sharon of messing with her head when she expresses her concerns.

Sharon and Kelly plan a trip to Kenya on behalf of a charity organization. Ozzy doesn't want them to go, as he fears they will be kidnapped or contract malaria. Sharon also has second thoughts after hearing more details about the trip. The family receives a visit from Sir Elton John, who gives Ozzy an expensive necklace that leaves him feeling a bit embarrassed; and goes on a shopping spree with Sharon, Jack and Kelly. Ozzy, Sharon and Kelly later attend an event in honor of Covenant House, where Sharon receives an award and Kelly bids on a puppy.

A 25-year-old fan wins a charity auction for the right to spend the day with Sharon. Sharon is touched by the woman's generosity and invites her to spend the night at the Osbourne home. Meanwhile, Jack must attend an online traffic school after getting a speeding ticket.

The family travels to Japan, where Ozzy is to receive the Legend Award at the Video Music Awards. Kelly also makes several personal appearances. One of the employees, Sam, meets with some family members whom he hasn't seen in years, but can only communicate with them through a translator.

Sharon's talk show tapes its final episodes. Feeling mistreated, Sharon clashes with her bosses to the very end, showing up late on purpose and demanding money upfront. She takes her mind off of things by shopping, including the purchase of a state-of-the-art toilet. Kelly feels hurt when Sharon repeatedly criticizes her wardrobe. Ozzy pays another visit to the dentist.

Dr. Phil McGraw pays a visit to the house, where he holds a frank discussion with the Osbournes about drug abuse and other issues that have affected the family's relationships with one another. Examples are given through clips from previous episodes.